Development of a Gas Chromatographic Scale of Solute Hydrogen Bond Acceptor Basicity and Characterization of Some Hydrogen Bond Donor Phases by Use of Linear Solvation Energy Relationships

Although there are hundreds of stationary phases available for gas chromatography, very few are even moderate hydrogen bond donors. In a search for strong hydrogen bond donor phases, we studied retention in some unusual liquids including two highly fluorinated alcohols, stearic acid, a fluorinated amide, and a phenolic phase. Retention data for more than 80 solutes spanning a very wide range in size, dipolarity, and hydrogen bond acceptor and hydrogen bond donor strength were examined. The results generally validate our previously developed method for measuring solute hydrogen bond basicity parameters. The retention data are well correlated by using solvatochromic linear solvation energy relationships based on a new set of GC-based solute parameters. Several strong hydrogen bond donor phases were identified, and their chromatographic properties were compared to solvatochromic properties measured by direct spectroscopic studies.